Users are increasingly utilizing electronic devices to transmit and receive information. In many instances, the users want or expect these transmissions to be secure. It is often the case, however, that these transmissions are able to be monitored or “snooped” during the transmission, whether by a governmental entity, malicious software, or another such source. Certain conventional approaches attempt to encrypt the communications in order to minimize the likelihood of the message contents being accessible during transport, but these approaches have various deficiencies. For example, communications can be encrypted at the message level, such as by using Pretty Good Privacy (PGP), whereby each party to a message must establish trust with the other parties to the message and must have the corresponding email encryption installed. These requirements have led to a high barrier to use and thus a relatively low level of adoption. Encryption can also be performed at the transport layer, where the encryption is performed by the mail servers rather than the end user. Using a protocol extension such as STARTTLS enables a plain text connection to be converted to an encrypted connection, such as may utilize the Transport Layer Security (TLS) or Secure Sockets Layer (SSL) cryptographic protocol. These approaches are best effort, however, meaning that the connection is not encrypted unless both mail servers to the connection support the extension. There is then no guarantee that the communication will remain encrypted in transit, such that the message may be susceptible to interception attacks.